
Vacation rentals with a pool in Roosevelt Roads
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Roosevelt Roads
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Amazing Infinity pool @Coqui Tropical House
Our family loved our time at Luis & Ivette's place during our family vacation. Luis reached out to us on day one to ensure we had a smooth check-in, offer suggestions for local restaurants and activities and introduce us to the neighborhood. The home was lovely and well-equipped. The outdoor space is fantastic for relaxing, grilling, and playing with children. Our granddaughter swam in the pool every day and we really appreciated all the games and pool toys that were available for her use. A wonderful place to stay with plenty of room for families.

Tropical Bliss House w/Pool
Was a pleasure to be host from Jose Anthony, you can’t expect more everything is very accessible from the house to the restaurants to the highway to go anywhere you have to go is right in the middle of every place And the host was always attentive and very friendly and respectful offering more than just the beautiful home but also getting back to us every time we have a question with perfect suggestions and always very friendly available

Home for 9 with Pool and Solar Panels in Vieques!
Beautiful place and wonderful host!

Luxury Casa CA-LI-AD
We stayed at Casa CA-LI-AD with two families (4 adults, 3 kids under 8) and had an amazing experience. The listing is accurate—everything was as described, clean, and very family-friendly. It’s close to the airport, attractions, and a supermarket, which made things super convenient. During our stay, there was a rare island-wide blackout, and the host went above and beyond to make sure we had what we needed. The property’s generator made a huge difference and gave us peace of mind. Pro tip: when using Uber, enter Casa CA-LI-AD with the dashes—otherwise it might not show up in the app. As a fellow Airbnb superhost, I can honestly say this place is exceptionally well cared for. Highly recommend for families!

Coastal Getaway with Pool, Game Room & Ocean View
Wonderful stay, beautiful place, can’t ask for anything more

Nena’s place, Carolina PR w electric generator
Great place and super clean!

La Casa Verde Luquillo (Green House Luquillo)
My friends and I stayed at this amazing Airbnb located right on Luquillo Beach. Seriously the most beautiful and quiet beach you will ever see. The pool was used basically everyday. It was nice to have a private area for us to use while we waited for other people to get ready for the day, or cool off after a long day of hiking and exploring the area. This air bnb is huge and honestly exceeded our expectations. The host was very responsive and friendly. There were even beach chairs and a beach cart for our use. He recommended lots of places and activites for us to do. CNote the Jazz bar is a must. Great location, we were able to either walk or drive everywhere. 25 minutes to the rain forest, 25 minutes to farajado. Highly recommend his place and location!

We are back! Puerto Rican paradise awaits you!
Rick is a superior host, kind and communicative! The house was everything we could wish for. Steps to a beautiful beach, and a private pool, gorgeous views! Just perfect!
Condo rentals with a pool

Isla Verde-Alambique Beach Modern Condominium
We had a wonderful stay at this charming home! It's in an ideal location—super close to the airport, which made our travel so much easier. The apartment was easy to find. The beach is just a short walk away and there are plenty of great restaurants nearby. The home itself was spotlessly clean and had a cozy, inviting atmosphere that made it feel like a true getaway. The balcony was nice. The check-in and check-out instructions were clear and easy to follow, making the whole process smooth and hassle-free. Highly recommend this place for anyone looking for a convenient and comfortable stay!

Relax in modern ocean condo with amazing 270° view
Second time we have stayed at this incredible place. The wind, the ocean, the rainforest- it is so beautiful. The condo is comfortable and AC in the bedrooms works great. We swam in the ocean and also enjoyed the pool at the condo! We love this place.

Ocean View Penthouse Condo with A/C in every Room
Excellent location, very quiet place, very comfortable for the family and for kids, beautiful view, beautiful surroundings, with a beach, a pool, a basketball and tennis court, too and a 10 minute walking distance from the "Malecón de Naguabo" where there are a lot of places to eat and very delicious. Hosts very responsive and proactive to help with everything! Thanks Diane and Luis for sharing this blessed place with us!

Lovely Ocean View Apartment
This unit is exactly as pictured with plenty of space, comfy beds and linens, a stocked kitchen and beautiful view. Cold AC in both bedrooms, but not in the living room. Secure building with elevators. Slightly dated but clean and well kept. Our only complaint was the location is next to a very busy marina, there is often noise and loud music from the boats and the restaurant next door but it stopped by midnight or so. Overall we were very pleased and would definitely stay here again!

Perfect Location 3bd2ba CondoVacation/Business
Brad & Juanita condo was just right bed was conftoble water pressure was good The location was perfect, with many beaches nearby and We enjoyed exploring the area and found plenty of great dining options nearby. , our experience was amazing. We would highly recommend

Beachfront Top Floor Condo next to Wyndham Hotel
This was our second time staying here and we loved it again! It fits our family of four so nicely. We can easily make meals and hang out on the balcony looking at the beautiful ocean or walk down and be right on the beach in minutes. We even reached out once to Tom noticing something was missing from the kitchen and he went to the store and brought it to us the very next day. Totally not expected and way above and beyond! We hope to come back next year and would definitely stay again if it is available.

Beachfront Paradise - 2 BR/BA Condo near El Yunque
Our group of 3 had a lovely stay. Host was helpful and the place was clean and comfortable. Having a pool and beach amenities (chairs, towels, boogie boards) was a huge plus along with the welcome snacks. The beach out front was not great for swimming (we were also there during a windy period so that made it harder), but it’s an easy drive to some other more protected spots. Nice restaurants are a short drive, and it’s easy to get to the rain forest for some cool hikes and adventures. Overall, we were very happy with the condo.

My paradise to you @ Aquatika
We absolutely enjoyed our stay! The pictures were good but the apartment looks better in person than in the pictures. Zenen and Wanda were very responsive and easy to get ahold of! We had a minor issue with the ac(ended up just being that the batteries in the ac remote needed to be changed) we contacted them and they fixed the issue within the hour! We appreciated how fast they responded to us. You can tell they actually care. Aquátika also is a lovely place. The landscaping & the pool areas were beautiful and clean. Aquatika also has 24/7 security & is gated so we felt extra safe! I definitely would recommend staying booking with Zenen and Wanda.
Quick stats about vacation rentals with a pool in Roosevelt Roads
Total rentals
90 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
3.8K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- Carolina Vacation rentals
- Culebra Vacation rentals
- Saint Thomas Vacation rentals
- Saint Croix Vacation rentals
- Tortola Vacation rentals
- Fajardo Vacation rentals
- Luquillo Vacation rentals
- Ponce Vacation rentals
- San Juan Vacation rentals
- Santo Domingo Vacation rentals
- Punta Cana Vacation rentals
- Las Terrenas Vacation rentals
- Condo rentals Roosevelt Roads
- Family-friendly rentals Roosevelt Roads
- Apartment rentals Roosevelt Roads
- Kid-friendly rentals Roosevelt Roads
- Rentals with a patio Roosevelt Roads
- House rentals Roosevelt Roads
- Rentals with outdoor seating Roosevelt Roads
- Pet-friendly rentals Roosevelt Roads
- Rentals with beach access Roosevelt Roads
- Rentals with a washer and dryer Roosevelt Roads
- Fitness-friendly rentals Roosevelt Roads
- Rentals with pools Machos
- Rentals with pools Ceiba Region
- Rentals with pools Puerto Rico
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Limetree Beach
- Distrito T-Mobile
- Morningstar Beach
- Carabali Rainforest Park
- Punta Bandera Luquillo PR
- Mandahl Bay Beach
- Hull Bay Beach
- Playa de los Cabes
- Inches Beach
- Playa Maunabo
- Playa Media Luna
- Playa Puerto Real
- Coco Beach Golf Club
- Playa de Cerro Gordo
- Toro Verde Adventure Park
- Luis Pena Beach
- The Saint Regis Bahia Golf Course
- Playa Vacia Talega
- La Fortaleza
- Punta Guilarte Beach
- Playa Mala Pascua
- Sun Bay Beach
- Vessel
- Las Paylas